Total Synthesis of Laingolide A Diastereomers

Pomey, Gaétan; Phansavath, Phannarath

doi:10.1055/s-0034-1380133

Cited by 9 publications

(2 citation statements)

References 6 publications

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“…40 was planned to be oxidized to carboxylic acid 39 , which had been reported before. However, the majority of examined one- and two-step procedures for the conversion of alcohol to carboxylic acid failed to deliver desired acid 39 . Only with a stepwise combination of IBX and Pinnick oxidation were we able to observe the formation of 39 as a mixture with carboxylic acid 41 , featuring additional oxidation at C14.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of Illisimonin A

et al. 2023

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The discovery of illisimonin A in 2017 extended the structural repertoire of the Illicium sesquiterpenoidsa class of natural products known for their high oxidation levels and neurotrophic propertieswith a new carbon backbone combining the strained trans-pentalene and norbornane substructures. We report an asymmetric total synthesis of (−)-illisimonin A that traces its tricyclic carbon framework back to a spirocyclic precursor, generated by a tandem-Nazarov/ene cyclization. As crucial link between the spirocyclic key intermediate and illisimonin A, a novel approach for the synthesis of tricyclo[5.2.1.01,5]decanes via radical cyclization was explored. This approach was applied in a two-stage strategy consisting of Ti(III)-mediated cyclization and semipinacol rearrangement to access the natural product’s carbon backbone. These key steps were combined with carefully orchestrated C–H oxidations to establish the dense oxidation pattern.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of Illisimonin A

et al. 2023

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“…One of the absolute configurations present in palmyrolide A was correctly assigned upon its initial isolation [ 15 ], and the absolute configurations of the remaining stereocentres were later established via total syntheses [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ]. The structurally intriguing laingolides have attracted considerable attention from the synthetic community [ 25 , 26 , 27 ]. In 2018, Dai and co-workers reported the first total synthesis of laingolide B and unambiguously assigned the absolute configuration as depicted in structure 4 [ 27 ] .…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Structural Reassignment of Laingolide A

Zhang

et al. 2021

Marine Drugs

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The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.

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Rh^II‐Catalyzed β‐C(sp²)−H Alkylation of Enol Ethers, Enamides and Enecarbamates with α‐Diazo Dicarbonyl Compounds

McLarney

Cavitt

Donnell

et al. 2016

Chemistry A European J

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A Rh -catalyzed method for intermolecular alkylation of the β-C(sp )-H bond of enol ethers, enamides, and enecarbamates with α-diazo-1,3-dicarbonyl compounds is reported. The products are formed in up to 99 % yield and can be readily derivatized under a variety of conditions. By utilizing a combination of experimental and computational studies, the presumptive addition-elimination reaction mechanism was investigated and found to proceed under thermodynamic control at higher temperature. The acquired fundamental knowledge was translated into a strategic reaction design and yielded the first example of the β-C-H functionalizations of acyclic enol ethers using α-diazo-1,3-dicarbonyl compounds.

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Total Synthesis of Laingolide A Diastereomers

Cited by 9 publications

References 6 publications

Asymmetric Total Synthesis of Illisimonin A

Asymmetric Total Synthesis of Illisimonin A

Total Synthesis and Structural Reassignment of Laingolide A

Rh^II‐Catalyzed β‐C(sp²)−H Alkylation of Enol Ethers, Enamides and Enecarbamates with α‐Diazo Dicarbonyl Compounds

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Total Synthesis of Laingolide A Diastereomers

Cited by 9 publications

References 6 publications

Asymmetric Total Synthesis of Illisimonin A

Asymmetric Total Synthesis of Illisimonin A

Total Synthesis and Structural Reassignment of Laingolide A

RhII‐Catalyzed β‐C(sp2)−H Alkylation of Enol Ethers, Enamides and Enecarbamates with α‐Diazo Dicarbonyl Compounds

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Product

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Rh^II‐Catalyzed β‐C(sp²)−H Alkylation of Enol Ethers, Enamides and Enecarbamates with α‐Diazo Dicarbonyl Compounds